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- Title
On the Manner of Cyclization of N-Acylated Aspartic and Glutamic Acid Derivatives.
- Authors
Zajdel, Paweł; Enjalbal, Christine; Żylewski, Marek; Subra, Gilles
- Abstract
When synthesizing arylpiperazine library modified with N-acylated amino acid derivatives (e.g., cyclized aspartic acid, cyclized glutamic acid, proline) we wished to rapidly determine the way of cyclization of N-acylated glutamic acid derivatives. During concomitant cleavage and cyclization two alternative routes were possible-either formation of six-member imide (glutarimide) or five-member lactam. Application of MS/MS and H NMR method allowed us to establish that cyclization of N-acylated glutamic acid derivatives preceded to lactams- N-acylated pyroglutamic acid derivatives. Graphical Abstract: Under acidic treatment the Lantern bound N-acylated glutamic acid derivatives underwent concomitant cleavage and cyclization. Herein, we studied two alternative cyclization routes-imides, lactams. It was found that cyclization of N-acylated glutamic acid derivatives yielded pyroglutamic acid derivatives (Structure C). [Figure not available: see fulltext.]
- Subjects
AMINO acids; ASPARTIC acid; GLUTAMIC acid; IMIDES; AMINES
- Publication
International Journal of Peptide Research & Therapeutics, 2011, Vol 17, Issue 2, p93
- ISSN
1573-3149
- Publication type
Article
- DOI
10.1007/s10989-011-9246-z